180 Interesting Questions to Ask Friends You Want to Know Better

Bypass the small talk and get to the deep stuff.

There are two goals to strive for in a new friendship: To learn more about the other person and to get them to like you. And according to researchers over at the Harvard Business Review, asking questions can help you accomplish them both. Other academics have even highlighted specific questions that can help accelerate the bond between two people. Certain prompts do a better job of uncovering specific personality traits and overcoming differences than others do.

Even if you disregard the science, asking questions of the other person when you're in a conversation is just good manners. It demonstrates a genuine interest in them, something sure to help evolve any relationship. So, whether you're trying to reconnect with an old pal or are in the process of getting to know a new connection better, be sure to keep reading below. We've put together an extensive list of the best questions to ask your friends.

RELATED: 206 Questions to Ask Your Crush to Learn Who They Really Are.

Questions to Ask Your Best Friend

two women walking and talking
  1. Did you have a good day?
  2. What's been weighing on you recently?
  3. What are you trying to prioritize during this chapter of your life?
  4. What's something you feel like you could use more support with?
  5. What are you most proud of about yourself?
  6. What's the next thing you want to cross off your bucket list?
  7. When was the last time you talked to your mom?
  8. When's the next time you're planning on visiting your family?
  9. Have you seen any good documentaries lately?
  10. What did you dream about last night?
  11. What are you having for dinner tonight?
  12. What's your current skincare routine?
  13. What's the next trip you want to take?
  14. Should we try to see each other more often?
  15. Are there any exciting new developments going on in your life?
  16. When was the last time you got sick?
  17. Do you have anything you need to get off your chest?
  18. Do you need help or advice with anything?
  19. Do you have any new book recommendations for me?
  20. What's your next big investment going to be?

RELATED: 236 Questions to Ask Your Girlfriend Before Getting Serious.

Fun Questions to Ask a New Friend

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  1. What's your favorite holiday?
  2. What's your favorite movie?
  3. What's your favorite season?
  4. Are you a night owl?
  5. Describe your ideal weekend.
  6. What's your favorite food?
  7. Do you watch a lot of TV?
  8. What was your favorite subject in school?
  9. What's your favorite form of physical exercise?
  10. What do you look for in a romantic partner?
  11. What's your favorite meal?
  12. Are you into astrology?
  13. Are you a punctual person?
  14. What was the first concert you ever went to?
  15. What's your biggest pet peeve?
  16. What are three words that describe you best?
  17. Can you describe your dream house?
  18. What's your ultimate comfort food?
  19. What was your last romantic relationship like?
  20. How would your friends describe you?

Juicy Questions to Ask Friends

three women sitting on a couch talking
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  1. Have you ever had a one-night stand?
  2. What's the most unusual request you've ever gotten in bed?
  3. Do you believe in love at first sight?
  4. Name a famous person you would ask your partner to give you a pass for.
  5. What was the most embarrassing thing you've ever done during a date?
  6. Have you ever been on a blind date?
  7. What's your love language?
  8. Have you ever accidentally texted something personal to the wrong person?
  9. How many people have you kissed?
  10. Do you think you're a good kisser?
  11. What's one thing that will turn you on instantly?
  12. What's your best advice for getting over a heartbreak?
  13. What's your grossest habit?
  14. Do you have any hidden piercings?
  15. What's the weirdest text you've ever received?
  16. Have you ever had a vacation fling?
  17. Have you ever been in love?
  18. Have you ever slid into someone's DMs?
  19. What's a relationship dealbreaker for you?
  20. How old were you when you got your first girlfriend/boyfriend?

RELATED: 200+ Get to Know You Questions That Actually Work.

Funny Questions to Ask Your Friends

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  1. What was your favorite game to play as a kid?
  2. What was your most embarrassing fashion moment?
  3. What do you need a crash course in?
  4. What's your favorite conspiracy theory?
  5. What's the best wifi name you've ever seen?
  6. What's the silliest fact you know?
  7. In 50 years, what do you think you'll be most nostalgic for?
  8. What's the best way to get rid of a hangover?
  9. When was the last time you fell down?
  10. What's the sexiest name you've ever heard?
  11. What's the best Tinder bio you've ever seen?
  12. What's your favorite type of cheese?
  13. Do you think mermaids give birth or lay eggs?
  14. What color has the worst personality?
  15. What gift would you give your enemy?
  16. Have you ever waved hello to the wrong person?
  17. Why is it called lipstick if it's not sticky?
  18. What's the most useless superhero power you can think of?
  19. Pineapple on pizza: Yes or no?
  20. Of all the fashion trends that have been popular over the past couple of years, which was the dumbest?

Questions to Ask Friends About Yourself

man and woman speaking at their desks
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  1. What's my best physical feature?
  2. What's your favorite memory of us together?
  3. What was your first impression of me?
  4. What do you think is my role in the friend group?
  5. Which one of your pet peeves do I aggravate most?
  6. What do you think is my best quality?
  7. How could I be a better friend?
  8. What's the weirdest thing about me?
  9. How do I generally smell?
  10. Am I good at giving advice?
  11. What's the most embarrassing memory you have of me?
  12. Which one of my boyfriends/girlfriends did you like the least?
  13. What's the dumbest thing I've ever done?
  14. Am I too competitive?
  15. Am I too stubborn?
  16. What's a skill of mine that you admire?
  17. What's something I've done or achieved that made you proud?
  18. What's one thing I could work on?
  19. When was the last time I really annoyed you?
  20. Am I a good travel buddy?

RELATED: 271 Questions to Ask Your Boyfriend Before Getting Serious.

Random Questions to Ask Your Friends

man and women discussing different questions to ask friends
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  1. What is the weirdest thing you've ever found in the woods?
  2. Do you have a hidden talent?
  3. When did you start shaving?
  4. Who is your favorite cartoon character?
  5. Who is the first person you text when you get good news?
  6. What's your favorite podcast?
  7. Are you handy?
  8. What's one song you want to play at your wedding?
  9. Who has the most dirt on you?
  10. What's your favorite fast-food chain?
  11. Have you ever laughed so hard that you peed your pants?
  12. What's the nicest thing you've ever done for someone else?
  13. Are you scared of heights?
  14. When was the last time you completed a jigsaw puzzle?
  15. How do you feel about cats?
  16. Do you have a green thumb?
  17. What's the craziest thing you've ever done?
  18. What's the biggest mistake you've ever made while dining out?
  19. What's the strangest thing you've ever seen someone do in public?
  20. What's the most unusual thing you've ever put in your mouth?

Deep Questions to Ask Your Friends

man and woman sitting on large concrete steps having a deep conversation
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  1. What's your biggest fear?
  2. What have your past relationships taught you about yourself?
  3. How do you define beauty?
  4. What's your biggest strength?
  5. Do you operate off logic or emotion?
  6. When was the last time you experienced jealousy?
  7. How do you define happiness?
  8. What keeps you up at night?
  9. What do you consider to be your personal calling?
  10. What's something that makes you feel spiritual or introspective?
  11. What's the most pressing political issue of our time?
  12. What do you wish you could change about your life?
  13. What's something you consider to be unforgivable?
  14. How do you typically deal with stress or frustration?
  15. What's been your greatest accomplishment?
  16. If you could give your younger self one piece of advice, what would you tell them?
  17. What's one activity that you find to be extremely beneficial for your mental health?
  18. What does your dream future look like?
  19. What book, movie, or piece of music has had the most impact on your life?
  20. What's one of the biggest life lessons you've ever learned?

RELATED: 21 Questions For a New Relationship.

Questions to Ask Your Friends About Their Jobs

man sitting at a conference table listening to a work pitch
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  1. What career path do you see yourself taking in the future?
  2. Describe your dream job.
  3. How do you define success?
  4. Have you ever befriended a co-worker?
  5. Do you have a good work ethic?
  6. What's the most rewarding thing about your job?
  7. Do you think you are adequately paid?
  8. How do you feel about company retreats?
  9. What's the nicest thing your boss has ever done for you?
  10. Do you have any funny stories from an office holiday party?
  11. What do you do at work daily?
  12. How did you achieve the position you currently hold?
  13. Do you prefer working remotely or in the office?
  14. What's the culture like at your company?
  15. How do you deal with difficult co-workers?
  16. Have you ever gotten fired from a job?
  17. Have you ever quit without notice?
  18. What was the biggest mistake you've ever made while on the clock?
  19. What is the most embarrassing interaction you've ever had with your boss?
  20. What are your career aspirations?

Interesting Questions to Ask Friends

man and woman walking arm and arm with their dog in a park
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  1. What's your favorite family tradition?
  2. What's your favorite family recipe?
  3. What's your earliest memory?
  4. What was your favorite extracurricular activity as a kid?
  5. Have you ever attempted a DIY home project?
  6. What was the name of your first childhood pet?
  7. Did you have a nickname growing up?
  8. What was your first word?
  9. What's your favorite movie to rewatch?
  10. Where did you go to school?
  11. What do/did you call your grandparents?
  12. Did you move around a lot as a kid?
  13. Do you have any famous people in your family?
  14. Have you ever had a fish tank?
  15. What's the coolest place you've ever visited?
  16. Did you have an imaginary friend growing up?
  17. What's one cultural tradition you'd like to pass on to your kids?
  18. Who was your favorite teacher in high school?
  19. Which of your family members are you closest with?
  20. What's your favorite childhood memory?

Important Things to Keep in Mind

Review the tips below before you start a conversation with any of these questions. They'll help you achieve the best possible outcome.

Don't forget about follow-up questions.

Typically, the goal of asking questions is to fall into a free-flowing conversation. To that end, ask follow-up questions to your friend's answers. This will help keep the dialogue fluid and prevent it from awkwardly fizzling out.

Try to keep things open-ended.

You never know where a conversation is going to go, and that's a good thing. Be flexible, and think of these questions more as conversation starters than something that might warrant an immediate and concrete response.

Pay attention to group dynamics.

Some questions are more personal than others. Pay attention to who is around and think about which questions you might want to save for when you and your friend have a moment alone. Also, try to put yourself in their shoes. Which questions would you want to answer in front of a large group of people and which would you want to reserve for a more intimate space?

Consider your timing.

Again, certain questions are heavier than others. Try not to get too personal too quickly, especially with someone who needs time to open up and get comfortable. Also, don't change the topic too quickly when someone shares something intimate. You also don't want to appear insensitive or disinterested.

Wrapping Up

That's it for our list of questions to ask your friends! Be sure to check back with us soon for more ways to break the ice. You can also sign up for our newsletter so you don't miss out on what's next!

Sources referenced in this article
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